4-[(2-Hydr­oxy-1-naphth­yl)methyl­idene­amino]benzoic acid

Mehmet Akkurt; Sema Öztürk Yıldırım; Abdullah Mohamed Asiri; Vickie McKee

doi:10.1107/S1600536808006107

. 2008 Mar 7;64(Pt 4):o682. doi: 10.1107/S1600536808006107

4-[(2-Hydroxy-1-naphthyl)methylideneamino]benzoic acid

Mehmet Akkurt ^a,^*, Sema Öztürk Yıldırım ^a, Abdullah Mohamed Asiri ^b, Vickie McKee ^c

PMCID: PMC2960922 PMID: 21202074

Abstract

The molecule of the title compound, C₁₈H₁₃NO₃, is almost planar, the dihedral angle between the naphthalene and benzene ring systems being 4.04 (6)°. The molecular conformation and packing are stabilized by intramolecular O—H⋯N and intermolecular O—H⋯O and C—H⋯O interactions.

Related literature

For background, see: Asiri & Badahdah (2007 ▶).

Experimental

Crystal data

C₁₈H₁₃NO₃
M _r = 291.29
Monoclinic,
a = 14.7490 (12) Å
b = 4.9850 (4) Å
c = 36.750 (3) Å
β = 91.305 (1)°
V = 2701.3 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 150 (2) K
0.31 × 0.19 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.970, T _max = 0.991
13445 measured reflections
3520 independent reflections
2761 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.145
S = 1.07
3520 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808006107/hb2705sup1.cif

e-64-0o682-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006107/hb2705Isup2.hkl

e-64-0o682-Isup2.hkl^{(210.4KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—HO1⋯N1	0.82	1.82	2.5572 (16)	148
O2—HO2⋯O3ⁱ	0.82	1.81	2.6281 (14)	171
C14—H14⋯O2ⁱⁱ	0.93	2.56	3.3611 (17)	145
C16—H16⋯O1ⁱⁱⁱ	0.93	2.49	3.1542 (19)	128

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

supplementary crystallographic information

Comment

2-Hydroxy Schiff base ligands and their complexes, derived from the reaction of salicylaldehyde and 2-hydroxy-1-naphthaldehyde with amines are of interest due to the existence of (O—H ···N and N—H ···O) type hydrogen bonds and tautomerism between the enol-imine and keto-enamine forms. Tautomerism in 2-hydroxy Schiff bases both in solution and in the solid state was investigated using different spectroscopic techniques (Asiri & Badahdah, 2007).

In the title compound, (I), the molecule is almost planar (Fig. 1). The maximum deviation of the non-H atoms from their mean plane is 0.087 (1) Å for O3. The dihedral angle between the naphthalene ring and the benzene ring is 4.04 (6)°.

The molecular conformation is stabilized by an intramolecular O—H···N hydrogen bond (Table 1). Then, classical inversion dimers are formed by head-to-head O—H···O linkages of the carboxylic acid groups. Finally, C—H ···O interactions link the dimers into sheets (Fig. 2).

Experimental

A solution of 4-aminobenzoic acid (5.0 g, 36.5 mmol) in hot ethanol was mixed with an ethanolic solution of 2-hydroxynaphthaldehyde (7.23 g, 36.5 mmol) and the resulting mixture was refluxed for 3 h. The mxiture was cooled to recover the crude product. Orange laths of (I) were recrystalized from ethanol. IR ν (cm^-1); 1683.3 (C?O), 1588.1 (C?N), 1427.1 (C?C), 1301.4 (C—O) and 1152 (C—N). [M.p.: > 573 K, yield: 54.7%].